SYNTHESIS OF 6,6-DISUBSTITUTED TETRAHYDROTHIOPHENO [3,4-C] ISOXAZOLINES FROM BETA-NITROENONES

Authors
AHRACH M SCHNEIDER R GERARDIN P LOUBINOUX B
Citation
M. Ahrach et al., SYNTHESIS OF 6,6-DISUBSTITUTED TETRAHYDROTHIOPHENO [3,4-C] ISOXAZOLINES FROM BETA-NITROENONES, Synthetic communications, 27(11), 1997, pp. 1865-1876
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
27
Issue
11
Year of publication
1997
Pages
1865 - 1876
Database
ISI
SICI code
0039-7911(1997)27:11<1865:SO6T[I>2.0.ZU;2-D
Abstract
beta-Nitrosulfides 2, formed by Michael addition of prop-2-en-1-thiol to beta-nitroenones 1 in the presence of a catalytic amount of triethy lamine, undergo either Intramolecular Nitrile Oxide Cycloadditions (IN OC) or Intramolecular Silylnitronate Cycloadditions (ISOC) to function alized 6,6-disubstituted tetrahydrothiopheno [3,4-c] isoxazolines 3 an d 4. The stereoselectivity, poor by the INOC reactions starting from a cyclic beta-nitroenones, is markedly increased with the ISOC procedure .